Work & Purpose

On a Mission to Turn Florida Retirees Into Entrepreneurs

Jean Cannon aims to make Sarasota a startup hub

Part of the America’s Entrepreneurs Special Report

Entrepreneurs are rightly celebrated for their innovations that change the rhythms of everyday life. For example, some members of widely dispersed families that came together for the holidays may have stayed at an Airbnb rental (founded in 2008), got around with Uber (2008) and made restaurant reservations online at Open Table (1998). Once the holidays are over, they might try to get back in shape at the fitness studio Soul Cycle (2006) and bring their holiday-strained finances into balance using the personal finance platform NerdWallet (2009).

Of course, the vast majority of entrepreneurial enterprises are far smaller than these now-megacompanies. And many startups fail. Still, business dreamers seem to be flourishing, at least in places like Silicon Valley, Austin, Texas and Boston.

Making Entrepreneurship Sprout in Sarasota

How about in, say, Sarasota, Fla., a county with one of Florida’s oldest populations — with a median age of 50+? Hardly, at least for now. But that may be about to change. One reason is Jean Cannon, who might single-handedly cause second-act entrepreneurship to sprout in Sarasota.

“We need to jump start entrepreneurship in our community,” says Cannon. “Our mentality is that the pie is only so big. We have to realize that we have to make the pie a little bit bigger.”

The majority of aging boomers will work beyond the traditional retirement age, and many will start businesses both for financial support and lifestyle.

— Intuit 2020 Report

If Cannon’s vision of Sarasota comes true, the area might become a hotbed of entrepreneurial activity.

If Cannon succeeds, I think other locales could take a page from her playbook to encourage their retirees to launch part-time businesses.

Let me tell you about Sarasota and what Cannon’s trying to do there.

Today, nearly a quarter of residents in the affluent city of Sarasota, on Florida’s southwestern coast, are 65 and older. The popular area’s rich cultural life and white sand beaches have long attracted retirees and tourists. But if Cannon’s vision of Sarasota comes true, the area might become a hotbed of entrepreneurial activity — the kind of place younger and older generations alike will gravitate to turn their ideas into commercial enterprises.

‘Retirement’ Is a Misnomer for Her

Cannon, a former high-tech veteran at firms such as Compuware and Bell Atlantic, retired from IBM in 2013. But to her, the word “retirement” is something of a misnomer. She’s out to build a virtual entrepreneurial ecosystem for her community through her new company, MyStartUpSunCoast.com. Her goal is for My Suncoast Startup to make it easy for entrepreneurs, investors and others to connect, find resources, share information and learn the nuts and bolts of building a business from scratch.

Like many switching from working at a large business to starting a company, however, Cannon had to learn to master many tasks on her own. For instance, she had a worldwide network of knowledgeable colleagues to tap into at IBM. But when I met her at her Sarasota townhouse, she was struggling to learn the web software program WordPress (popular with bloggers).

Wearing Four Hats

She’s already taught herself to become familiar with Facebook, Mailchimp and other programs critical to modern entrepreneurs. “It’s not difficult, but it’s a lot when you’re wearing four to five hats,” she laughs.

Cannon plans on eventually taking outside investors. She is currently looking for a business partner to speed the growth of the business, and developing relationships with entrepreneurs and local small business organizations. One question she’s pondering for her site, and one that many entrepreneurs wrestle with: “What are customers willing to pay?”

Cannon’s venture is laudable and highlights one of the more encouraging trends in the economy: A stirring in new business creation. The nation’s overall startup rate was in decline even before the Great Recession sent new business creation plummeting to its lowest level in nearly two decades in 2014, according to the Kauffman Foundation. But Kauffman’s data shows that entrepreneurial activity has picked up, along with the economy, over the past two years.

Cities, counties and towns throughout the country are putting more resources into nurturing small business creation. Just look at the rise in co-sharing workspaces, incubators and accelerators.

The Boom in Older Entrepreneurs

What’s more, older Americans are embracing entrepreneurship in growing numbers, contrary to widespread expectations that entrepreneurship would decline with age.

Kauffman’s 2016 Index of Startup Activity says that individuals age 55 to 64 account for 24 percent of all new entrepreneurs, up from about 15 percent in 1997. As the Intuit 2020 Report by the software company Intuit and the small business consulting firm Emergent Research put it: “The majority of aging boomers will work beyond the traditional retirement age, and many will start businesses both for financial support and lifestyle.”

The state of American entrepreneurship may actually be healthier than some of the “official” statistics. Reason? The legions of self-employed and independent operators with multiple gigs, particularly older workers in the second half of life who are looking for meaning and money.

“Business founders are as diverse as the population,” says David Deeds, the Schultze professor of entrepreneurship at the University of St. Thomas in Minneapolis.

For Love and Money

Deeds advises retirees to “do something you love and make some money at it.” In a sense, that’s what Sarasota artist Kevin Costello does. He’s someone who’d make Cannon proud.

Costello emigrated from England to the U.S. in the early ‘70s and then taught at places like the San Francisco Academy of Art and the San Francisco Museum of Modern Art. He moved to Florida in the ‘80s and taught at the Ringling College of Art and Design in Sarasota. Throughout his career, he has created large-scale sculptures, paintings, drawings conceptual photography and other art. (You can admire his portfolio at KevinCostelloArt.com.)

These days, when not making art, Costello lectures in the elderhostel program at Stetson University and teaches at Pierian Spring Academy and the Adult and Community Enrichment Department of Sarasota County Technical Institute. In other words, he’s an entrepreneur with a portfolio of activities that provide purpose and a paycheck. “Artists don’t retire,” Costello says. “I don’t see an end to what I am doing. I enjoy it. Why do something else?”

Isn’t that what we all want to be able to say at any age?

Entrepreneurship isn’t easy. Nor is it for everyone. But it has opened opportunities for creativity and meaning for Cannon and Costello and might for you, too.

I think entrepreneurship may well become the most common business card among an aging population. If so, that’s both good for the economy and for society.

Chris Farrell
By Chris Farrell
Chris Farrell is senior economics contributor for American Public Media's Marketplace. An award-winning journalist, he is author
 of the books Purpose and a Paycheck:  Finding Meaning, Money and Happiness in the Second Half of Life and Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community, and The Good Life.@cfarrellecon

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